In a situation when a man will both be lighting the Yom Tov candles and making Kiddush, when should he make Shehecheyanu?
Do we say only when lighting candles, since that is when the women say it when they light candles (and perhaps because that is the earliest possible opportunity)?
Do we say that they should only say it when making Kiddush, since that is when it would normally be said?
Or, are there certain times when men would say the blessing both times, such as when the Shehecheyanu in Kiddush also applies to another Mitzvah of the day. For example, would the man say Shehechyanu both when lighting the candles on the second day of Rosh Hashana, and during Kiddush when we are supposed to have in mind a new fruit or garment when saying the Shehecheyanu (Orach Chaim 600:2)?
And, assuming the man is supposed to say it twice, what does he do if already said it when he lit the candles and he doesn't have a new fruit or garment? (Normally Shulchan Aruch says to say it anyway, but in this case he has already said it when he lit the candles)
Take Sukkot as an example. The Shulchan Aruch (Orach Chaim 641:1) tells us that the Shehecheyanu we say on the first night of Sukkot is also being said for the Sukkah. If for some reason you said Shehecheyanu on the first night of Sukkot outside the Sukkah you repeat it the first time you sit in the Sukkah. If so, it would stand to reason that if the man said it when he lit candles he would still repeat it when making Kiddush in the Sukkah. In such a situation, should the man skip it when he lights candles and only say it in Kiddush, or should he say it twice?
Answer
Say it only during kiddush. The women too should only say it during kiddush. Why would one assume the two would be any different? They are both obligated in kiddush and both obligated to have the lights lit. The Talmud in Sukkah (47b) implies already that the shehechiyanu is said with the kiddush. (The Tur OC 519 deems it an "enactment of [the sages] to say it [then].") I see no reason to distinguish between genders.
Some more discussion: The Mishna Brurah (263:23) and Rav Moshe Feinstein (Igros Moshe OC 4:101) both point out that the custom of some women to say shehechiyanu when lighting has no basis, but one does not need to protest against women who do so. Moreover, Rav Ovadiah Yosef (Yechavveh Da'at 3:34) actually recommends stopping the practice because it is preferable to say the shehechiyanu on kiddush (and quotes a slew of opinions who agree with him, as he is wont to do). The only reason it seems that no one has fully condemned the practice is because everyone agrees that the bracha is not levattala: the gemara referenced above explicitly permits one to say shehechiyanu while standing in the market and this is indeed what most men do on Yom Kippur. But it is clear that the ideal time is to say it with kiddush.
I'm not sure why one would continue to teach their daughters this minhag. But all the more so why a man who happens to be lighting candles one yom tov would give up the shehechiyanu on kiddush for candles when there is no reason for him to do so!
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